This is a style of shoe that has become synonymous with artists and rock starts (namely The Beatles). The Chelsea boot, with its heritage-inspired look, adds dimension to a man’s wardrobe, with its sleek, clean lines lending themselves nicely to the fitted attire that is so prevalent in menswear today. It’s an old school shoe with new school swag.

Dr Martens Original Chelsea Boots
Buy now for $130 at Asos

Wolverine 1883 Garrick Chelsea Boots
Buy now for $165 at Amazon

Base London Combust Leather Chelsea Boots
Buy now for $135 at Asos